The New York Yankees' 10 Most Painful Postseason Losses

Few would argue the point that the Yankees are the most successful franchise in the history of American professional sports. In the past century, they’ve won 27 World Championships and 40 American League Pennants, while making the postseason 51 times.

But where there are legendary victories, unfathomable comebacks and series-clinching home runs, there are also epic defeats—games where someone else came out on top, and the Yankees and their fans were left in stunned disbelief, wondering what went wrong.

The following are the worst of the worst—ten gut-wrenching losses whose memories have made winning all the more sweet for the team from the Bronx.

Game 7 of the 2004 ALCS was really just the culmination of the most painful four days in Yankee history, but the Red Sox celebrating on the hallowed turf of the old stadium after completing the greatest postseason comeback ever was the most brutal single moment.

The Yankees took a commanding and seemingly insurmountable 3-0 series lead with a 19-8 drubbing of the Red Sox in Game 3 at Fenway Park. Then, six outs from the World Series, in game four, Mariano Rivera blew a save on a single by Bill Mueller. The Red Sox came back again in Game 5 to force the series back to New York. Curt Schilling won the “bloody sock” battle in Game 6, and things were all tied up.

In Game 7, the Yankees started 38-year-old Kevin Brown, who’d given up four runs in just two innings in Game 3, on short rest. Brown was predictably awful, allowing a two-run homer to David Ortiz in the first, then loading in the bases in the second before being removed.

With Johnny Damon up and the game in the balance, Yankee manager Joe Torre called on, not a lefty reliever to neutralize him, but rather Javier Vazquez, who’d allowed 33 home runs during the regular season, 20 of which were slugged by left-handed hitters. Damon promptly deposited a grand slam into the upper deck in right. Derek Lowe had little trouble with the Yankee offense, and the next seven-and-a-half innings turned into a party for the Red Sox and their fans.

In losing Game 7, the Yankees lost not only the ALCS, but also their long-held upper hand in sports’ greatest rivalry. Boston swept St. Louis to claim its first World Series crown since 1918. It would be five years before the Yankees would make it back to the Fall Classic.

The 1960 World Series was a battle of two teams that couldn’t have been much more different. The Yankees had won eight of the previous thirteen championships and had captured AL pennants in 10 of those seasons. The Pirates had improved by 21 wins from ‘59 to ‘60 and were seeking their first title in 35 years. Their seven game classic would wind up etched in the annals of baseball lore.

The first six games of the contest were a wild ride, with the Yankees securing Games 2, 3 and 6 by a combined margin of 35 runs, powered by 18 scoreless innings and two victories by Whitey Ford. The Pirates, meanwhile, squeaked out their three wins, two by Vern Law and one by Harvey Haddix. It all set up a winner-take-all bout at Pittsburgh’s Forbes Field, where Law returned for his third start against Yankee hurler Bob Turley.

The game was anything but a pitcher’s duel. The Pirates jumped out to an early 4-0 advantage on a two-run homer by Rocky Nelson in the first and a two-run single by Bill Virdon in the second. The Yankees got on the scoreboard in the fifth thanks to a Moose Skowron solo blast. Then a four-run rally in the sixth gave them their first lead. New York added two more runs in the eighth, and found itself ahead by three, six outs from victory.

But game seven was far from over. Pittsburgh bounced back in the bottom of the eighth, scoring five in a frenzy capped by a Hal Smith three-run blast. In the top of the ninth, the Yankees responded. Bobby Richardson and Dale Long hit back-to-back singles off Bob Friend to put the tying runs on base. Friend was replaced by Haddix, who retired Roger Maris on a pop fly but then surrendered the lead on a Mickey Mantle single and a well-placed grounder by Yogi Berra.

With the game tied 9-9, Ralph Terry took the mound for the Yankees in the bottom of the ninth. Slap-hitting second baseman Bill Mazeroski stepped to the plate and launched arguably the most famous home run in baseball history.

Mazeroski’s blast was the first time the World Series ended on a home run, and one of just two such occurrences to this day. Ironically, it was the Yankees’ second baseman, Bobby Richardson, who was named series MVP, the only player ever to earn that honor in a losing effort.

The 2001 World Series could have been remembered as the greatest ever for the Yankees if things had gone just a little differently.

In search of a four-peat, and just weeks after New York’s darkest day, the Yankees were accomplishing some of their most astonishing postseason feats. They came back from being down 2-0 against the Oakland A’s, in a series that turned on Derek Jeter’s famous “flip play.” They squashed the Seattle Mariners, who’d won an American League record 116 regular season games in the ALCS. Then Tino Martinez and Scott Brosius hit two-out, bottom-of-the-ninth, game-tying two-run homers off Diamondbacks closer Byung-Hyun Kim on back-to-back nights in Games 4 and 5 of the World Series.

After Randy Johnson gave the Yanks a stern talking to in Game 6, Roger Clemens took the mound against Curt Schilling in Arizona for the decisive Game 7. Both starters were at their best, and after seven, the contest was tied 1-1. In the top of the eighth, Alfonso Soriano hit a homer to give New York the lead. Mariano Rivera entered the game in the bottom of the inning and sat the D-Backs down in order, placing the Yankees three outs from victory.

Then things got weird. Mark Grace led off the bottom of the ninth with a single. When Damian Miller bunted, Rivera fielded and threw wildly to second and everyone was safe. The bunt play was on again. This time, Rivera made a fine throw to third to force the lead runner, but Scott Brosius held the ball rather than going for a double play at first. Tony Womack lifted a blooper over first that landed on the right field foul line for a game-tying double. With runners on second and third and one out, the Yankees brought the infield in. Luis Gonzalez punched a soft humpbacked liner over Jeter, and the D-Backs were champions.

Ironically, losing Game 7 of the 2001 World Series saved the life of utility infielder Enrique Wilson. Wilson originally had a seat booked on American Airlines flight 587 from New York City to his native Dominican Republic, which crashed into Rockaway, Queens on November 12th, killing everyone on board. Since the Yankees did not win and there was no victory parade, Wilson decided to go home a few days early and changed his flight.

4. October 10th, 1926: World Series Game 7: St. Louis Cardinals 3, NY Yankees 2

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For most baseball fans, the go-to answer to the question “Who was the greatest team of all time?” is “The ’27 Yankees.” Maybe the team’s 110-win World Championship season, powered by a lineup that would become known as "Murderer’s Row," was in part spurred on by the way their 1926 campaign ended.

Behind Babe Ruth, Lou Gehrig, Tony Lazzeri and company, the Yankees took a 3-2 lead over the Cardinals through five games. They traveled to St. Louis, where they hoped to close things out, but the trip didn’t go as planned. The Bombers were walloped in Game 6 by a score of 10-2, shut down in a complete-game masterpiece by a 39-year-old Grover Cleveland Alexander, whom the Cards had dealt for during the season.

In Game 7, the Yankees trailed 3-2 in the seventh, when St. Louis starter Jesse Haines was replaced by Alexander coming out of the pen on no days rest to finish the job. “Old Pete” stymied the Yankee bats once again, retiring the first seven men he faced before walking Ruth with two outs in the ninth. Bob Meusel stepped to the plate as the go-ahead and possible series-winning run, but he never got the chance to do damage. Ruth took off for second and was gunned down by Cardinals catcher Bob O’Farrell, giving St. Louis the victory and the championship.

Ruth did steal nine bases in 1926, and he certainly wasn’t the lumbering oaf he’s often portrayed as in popular media. Still, to attempt a steal of second with two outs in the ninth was ill-advised at best. Ruth’s blunder is the only time a World Series has ever ended with a baserunner being caught stealing.

Alexander’s two-win, one-save performance in the ’26 World Series is considered one of the great postseason performances of all time and, arguably, the crowning achievement of his Hall-of-Fame career. The Cardinals are the only team that has met the Yankees more than once in the World Series and has a winning record.

When the Yankees won the inaugural American League wildcard in 1995, it was their first postseason appearance in 14 years and the first ever for captain and fan-favorite Don Mattingly. After a slow start to the season, the team went 49-29 after the All-Star break to capture the playoff berth and, in the ALDS, took on the Mariners, who finished the season on a torrid streak of their own to grab the AL West crown in a one-game playoff victory over the Angels.

The series started off well enough for the Yankees. Mattingly’s hot hitting and a Game 2, 15th inning walk-off homer by Jim Leyritz staked them to a 2-0 series lead heading to Seattle. But the Kingdome would soon become a house of horrors for New York. The Ms scored 18 runs off Yankee pitching in Games 3 and 4 to tie the series, setting up a series-deciding Game 5.

The Yankees clung to a 4-2 lead in the bottom of the eighth, thanks to a two-run homer by Paul O’Neill and a two-run double by Mattingly, when starter David Cone ran into trouble. He allowed a solo homer to Ken Griffey Jr., before losing the lead on a bases loaded walk. After 147 pitches, the fourth most in postseason history, Cone was finally pulled and replaced by a young converted starter named Mariano Rivera. In the ninth, Seattle manager Lou Piniella called on Randy Johnson on one day of rest, and Yankee skipper Buck Showalter countered with his own Game 3 starter, Jack McDowell.

The game remained tied until the 11th, when Randy Velarde singled in Pat Kelly to give the Yankees a tenuous 5-4 lead. Instead of going to his closer John Wetteland, who’d been pounded for seven runs in four innings in the series, Showalter stuck with McDowell in the bottom of the frame. Joey Cora and Griffey started things off with back-to-back singles before Edgar Martinez, one of the great Yankee-killers, doubled to left, plating both runners with the tying and winning runs.

At the time, no one knew that the Yankees would go on to win four of the next five World Championships, but that night in Seattle marked a bitterly disappointing end to Showalter’s tenure as Yankee manager and to Mattingly’s career.

Prior to 1955, the Yankees and Brooklyn Dodgers had faced off five times in the World Series in the preceding 14 years, and the Yankees had won all five meetings. The Dodgers were 0-7 all time in Fall Classics, while the Yankees were a menacing 16-4.

For the first six games of the ’55 series, the home teams were dominant, with the Yankees taking the first two in the Bronx and the Dodgers grabbing the next three at Ebbets Field in Brooklyn. After leveling the series on a complete-game four-hitter by Whitey Ford in Game 6, the Yankees had to feel good about the decisive contest. They sent game two winner Tommy Byrne to the hill against a 23-year-old Johnny Podres.

The Dodgers took the lead in the fourth when Roy Campanella doubled and Gil Hodges singled him in. They struck again in the sixth, loading the bases, and then scoring on a Hodges sacrifice fly. The Yankees did their best to rebound in the bottom of the inning. Billy Martin walked, then Gil McDougald reached on a bunt single. But the rally died on one of the more famous defensive plays in World Series history. Yogi Berra stroked a line drive to left that would likely have tied the game had it fallen in. Instead, Sandy Amoros, who’d entered the game as a defensive replacement chased the ball down, then fired to first to double up McDougald. The Yankees would threaten again in the eighth by putting runners on first and third, but Podres escaped the jam, then mowed the Bombers down on the ninth to give Brooklyn its first title.

No longer was the Yankee-Dodger rivalry one of the hammer meets nail variety. The Yanks would get their revenge a year later, besting Brooklyn in another seven-game classic that featured Don Larsen’s perfect game, before the Dodgers left New York for southern California in 1958. The two teams went on to split four bi-coastal World Series’ between 1963 and 1981.

7. October 12th, 1962: World Series Game 5: St. Louis Cardinals 5, NY Yankees 2

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Most Yankee fans know Tim McCarver as that commentator on FOX who says “in my view” a lot and seems to root against their team. Not everyone remembers that McCarver is also responsible for one of the more crushing home runs hit against New York in the World Series.

After being swept in the ’63 Fall Classic, the Yankees, under manager Yogi Berra, were looking to reclaim their place atop the baseball world in ’64. They took on the Cardinals, who overcame a six-and-a-half game deficit with 12 games to go to swipe the NL Pennant from the Phillies. The teams split the first two games in St. Louis, and then the next two in New York to set up a pivotal Game 5, a key contest for the Yanks, who didn’t want to return to the Midwest facing elimination.

The Yankees tagged Mel Stottlemyre to start versus future Hall-of-Famer Bob Gibson. Stottlemyre had won the same matchup in Game 2, but this time, Gibson was at his best. The starters traded goose eggs for four innings until the Cardinals broke through for two runs in the fifth. Gibson would not relent, allowing just three hits while striking out 11 through the first eight innings. The Yankees came to bat in the ninth with their backs against the wall. Mickey Mantle reached base on an error by St. Louis shortstop Dick Grout. Then, with two outs, Tom Tresh smacked a homer over the fence in right-center to tie the game.

The Yankees’ jubilation was short lived. In the top of the tenth, Bill White walked and Ken Boyer bunted for a hit, setting the table for McCarver’s at bat against reliever Pete Mikkelsen. The Cards’ catcher blasted a home run to right, giving St. Louis a commanding three-run lead. Gibson came out for the bottom of the tenth and set the Yankees down with ease, scoring the final out on a Roger Maris foul pop-up to Boyer.

While the Yankees were able to snag Game 6 to re-tie the series, Gibson returned on two days rest in Game 7 to slam the door on New York. ’64 turned out to be the last hurrah for the Mantle-era Yanks, and 12 long years passed before they appeared in the World Series again. Bob Gibson managed to top his 13th strikeout performance a few years later when he K’d 17 Tigers in Game 1 of the ’68 Classic. He pitched an astounding eight complete games in World Series play and is remembered as perhaps the greatest October pitcher of all time.

After squeaking out a five-game division series win over the the Orioles, despite an anemic offensive effort, the Yankees limped into the ALCS versus Detroit, hoping to turn things around. They didn’t. In Game 1, Tiger starter Doug Fister held the Yankee lineup scoreless through six plus innings before turning it over to the bullpen.

Andy Pettitte did his best to match Fister’s mastery, but he surrendered two runs in the sixth, and relievers Derek Lowe and Boone Logan combined to allow two more in the eighth. In the bottom of the ninth, the Yankees trailed 4-0, and Detroit manager, Jim Leyland, brought in his fist-pumping closer Jose Valverde.

Russell Martin led off with a single and was brought in on an Ichiro Suzuki home run that closed the gap to 4-2. With two outs and Mark Teixeira on first, Raul Ibanez, who’d won game three against the Orioles by hitting both game-tying and game-winning home runs, stepped to the plate. In what could have been one of the great moments in Yankee lore, Ibanez sent Valverde’s first pitch into the right field stands, tying the game.

But the Yankees couldn’t deliver the finishing blow. For the next three innings, they dove back into their offensive malaise before the Tigers finally took the lead in the 12th on a Delmon Young double. Things got worse. Derek Jeter fell while chasing a Jhonny Peralta grounder on what was later revealed to be a broken ankle that ended his season.

The Yankees went down meekly in the bottom of the 12th, and Detroit went on to win the next three in dominant fashion, never allowing New York a lead. It was the first time the Yankees had been swept in a playoff series in 32 years.

9. October 10th, 1980: ALCS Game 3: Kansas City Royals 4, New York Yankees 2

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The Yankees and Royals once had a pretty fierce rivalry, which spanned from Chris Chambliss’ ALCS-winning home run in 1976 through the “pine-tar game” in 1983. Between 1976 and 1980, the two teams battled for a trip to the World Series four times in five years, with the Yankees taking each of their first three playoff meetings.

In 1980, the Royals were determined to pull out a different outcome. They took the first two games, hitting Ron Guidry hard in Game 1 and snatching a 3-2 nail-biter in Game 2. But the Yankees were confident, heading home to the Bronx for the final three games, where they’d scored big postseason wins over Kansas City before.

Behind a strong performance from Tommy John, the Yankees took a 2-1 lead into the seventh, when manager Dick Howser called on flame-throwing closer Goose Gossage with a runner on second and two out. Gossage gave up a single to U.L. Washington, which brought up George Brett, who hit .390 in 1980 and would soon be named the AL MVP. Brett sent a Gossage fastball soaring into the upper deck of Yankee Stadium, stunning the crowd and granting the Royals a 4-2 lead.

In the bottom of the eighth, the Yankees loaded the bases with no one out versus Royals closer Dan Quisenberry, thanks to Bob Watson's triple and walks to Reggie Jackson and Oscar Gamble. But Rick Cerone hit a line drive right at the shortstop Washington, who doubled Jackson off second base. The Yankee bats would not be heard from again, and Kansas City went on to face the Phillies in the World Series.

After staking an uneventful claim to the AL wildcard, the Yankees entered the 1997 postseason riding high as the reigning champions of baseball. Many fans overlooked the first round matchup with the 86-win Indians, thinking ahead to either a rematch of the ’96 ALCS vs. the Orioles or a shot at revenge for the Yanks’ ’95 ALDS loss to the Mariners. But even with stars like Albert Belle and Kenny Lofton gone to Chicago and Atlanta respectively, Cleveland proved they were no afterthought.

The two teams split the first two meetings in the Bronx then moved on to Jacobs Field for the final three contests in the best-of-five. The Yankees grabbed Game 3 on a typically strong October performance by David Wells and hoped to close things out in Game 4. In a matchup that looked like a throwback to the late 80s, they sent Dwight Gooden to the hill against Orel Hershiser.

The Yankees jumped ahead in the first, thanks to RBI hits by Paul O’Neill and Cecil Fielder. Though those were the only runs they scored, Gooden was sharp, allowing just one run in six innings of work. When Jeff Nelson and Mike Stanton combined to strike out the side in the seventh, the Yankees looked to be in good shape. With one out in the eighth, Joe Torre called on Mariano Rivera, who’d saved 43 games with a 1.88 ERA in his first season as closer. Rivera got Matt Williams on a fly out to right, but then catcher Sandy Alomar Jr. stepped in and knocked a game-tying homer into the seats in right.

With the game still tied, Torre brought in Ramiro Mendoza for the ninth, foregoing a second inning of Rivera. Marquis Grissom led off with a single and moved to second on a Bip Roberts sac bunt. Omar Vizquel hit a grounder up the middle that barely eluded Derek Jeter’s outstretched glove. Grissom scored, and the series was tied at two.

In Game 5, Cleveland took an early lead, and postseason hero Jaret Wright made it hold up, dashing the Yankees’ hopes of a repeat. The Indians went on to suffer an epic loss of their own in Game 7 of the World Series, where they were beaten by the Florida Marlins in an extra-inning marathon.